HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonium Chloride → 9H-fluoren-9-ylmethyl (3S,5R)-3-hydroxymethyl-5-(3,4,5-trifluorophenyl)morpholine-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 9-Fluorenylmethyl chloroformate | HCID 34367 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | [(3S,5R)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]methanol | HCID 67373759 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 9H-fluoren-9-ylmethyl (3S,5R)-3-hydroxymethyl-5-(3,4,5-trifluorophenyl)morpholine-4-carboxylate | HCID 67373263 | 99% |
Reaction Steps
9-Fluorenylmethyl chloroformate (327 mg) was added to a mixed solution of [(3S,5R)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]methanol (250 mg) in dichloromethane (5 mL) and a saturated sodium bicarbonate solution (5 mL), and the reaction solution was stirred at room temperature for six hours. Dichloromethane and a saturated ammonium chloride solution were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: heptane->heptane:ethyl acetate=2:1) to obtain 470 mg of the title compound. The property values of the compound are as follows.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08048878B2 |
| Source dataset | uspto-grants-2011_11 |
| ORD ID | ord-8bf7ad4ff91b48c19369939401fb287a |
| Source note | uspto-grants-2011_11 |